The department store chain saw its share price tumble to 4.68p on the first day of trading in 2019, ahead of an update due on 10 January.
The falling shares come as Debenhams struggles to adapt to challenging retail conditions. In its 2018 annual report the chain reported a loss of £491.5m, the worst in its history.
Ashley slammed the Debenhams board for rejecting his offer of a £40m loan, a move that was widely seen as an attempt to take control of the business.
The sliding shares suggest investors have low expectations for the company’s Christmas trading.
“Pictures on social media of the retailer’s messy shelves and the usual widespread discounts on goods people don’t really want in the first place would suggest that Debenhams continues to be stuck in a rut,” said Russ Mould, investment director at AJ Bell.
Retail shares took a hit in December after a profit warning from online retailer Asos sparked a sell-off of fashion stocks across Europe.
Investors will be keeping a close eye on upcoming trading updates for an indication of how much retailers have struggled over the Christmas period.
Clothing retailer Next will release its trading update tomorrow, while Marks & Spencer, JD Sports and Primark owner Associated British Foods are due to publish their festive figures in the coming weeks.
Debenhams, which has seen its value fall to £57m, has announced plans to close 50 stores across the UK in an attempt to cut losses.
“The UK winner of the £115 million Euromillions jackpot on New Year’s Day could buy Debenhams and still have half their money left over,” said Mould.
“However, it seems fair to suggest that wouldn’t be the best way to spend their winnings given the company is drowning in debt and has a business model which is increasingly irrelevant in the modern world of retailing.”